IP Library Granted Patent US 9,276,217
Granted Patent B2
US 9,276,217 · App. 13/989,253 · Granted Mar 1, 2016

Electroactive materials

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,276,217
App. No.
13/989,253
Granted
Mar 1, 2016
Kind
B2
Abstract

There is provided an electroactive compound having Formula I In the formula: Ar 1 , Ar 2 , and Ar 3 are the same or different and are aryl groups; R 1 is the same or different at each occurrence and is D, alkyl or aryl; a is an integer from 0-4. The compound has a LUMO level deeper than −2.3 eV and a band gap of at least 2.9 eV.

Claims (39)

1. An electroactive compound having Formula II

wherein:

Ar 1 is an aryl group;

R 1 is the same or different at each occurrence and is D, alkyl or aryl;

R 2 is an electron-withdrawing group;

R 3 is H, D, carbazolyl, diarylamino, an electron-withdrawing group, or a deuterated analog thereof;

R 4 is the same or different at each occurrence and is cyano, nitro, or —SO 2 R, where R is alkyl, or a deuterated analog thereof;

R 5 is the same or different at each occurrence and is D, alkyl, alkoxy, silyl, siloxane, an electron-withdrawing group, or a deuterated analog thereof;

a is an integer from 0 to 4;

b is an integer from 0 to 4;

c is an integer from 1 to 5;

d is an integer greater than 0, such that c+d≦5; and

e is an integer from 0 to 4

and further wherein the compound has a LUMO level deeper than −2.3 eV and a band gap of at least 2.9 eV.

2. The compound of claim 1 , wherein Ar 1 is phenyl, biphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, a substituted derivative thereof, or a deuterated analog thereof.

3. The compound of claim 1 , wherein R 1 =D and a and b are both greater than 0.

4. The compound of claim 1 , wherein R 2 is cyano, nitro, or —SO 2 R, where R is alkyl.

5. The compound of claim 1 , wherein R 3 is carbazolyl, diphenylamino, or a deuterated analog thereof.

6. The compound of claim 1 , wherein e=0.

7. The compound of claim 1 , wherein d=1 and R 2 ═R 4 ═CN.

8. A compound selected from compound B1 through B11

9. An organic electronic device comprising a first electrical contact, a second electrical contact and a photoactive layer therebetween, the photoactive layer comprising an electroactive compound having Formula II

wherein:

Ar 1 is an aryl group;

R 1 is the same or different at each occurrence and is D, alkyl or aryl;

R 2 is an electron-withdrawing group;

R 3 is H, D, carbazolyl, diarylamino, an electron-withdrawing group, or a deuterated analog thereof;

R 4 is the same or different at each occurrence and is cyano, nitro, or —SO 2 R, where R is alkyl, or a deuterated analog thereof;

R 5 is the same or different at each occurrence and is D, alkyl, alkoxy, silyl, siloxane, an electron-withdrawing group, or a deuterated analog thereof;

a is an integer from 0 to 4;

b is an integer from 0 to 4;

c is an integer from 1 to 5;

d is an integer greater than 0, such that c+d≦5; and

e is an integer from 0 to 4

and further wherein the compound has a LUMO level deeper than −2.3 eV and a band gap of at least 2.9 eV.

10. The device of claim 9 , wherein the photoactive layer comprises the electroactive compound of Formula II and further comprises a host material.

11. The device of claim 9 , wherein the photoactive layer consists essentially of the electroactive compound of Formula II and a host material.

12. The device of claim 9 , wherein the photoactive layer comprises a blue luminescent compound, a host material, and a compound having Formula II.

13. The device of claim 9 , wherein the photoactive layer consists essentially of a blue luminescent compound, a host material, and a compound having Formula II.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: LG CHEM, LTD.
Reel/Frame 050150/0482 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 29, 2013
From: GAO, WEIYING; HERRON, NORMAN; GUIDRY, MARK A.
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 030503/0918 →